Sicily is larger than many first-time visitors expect, and the distances between towns are longer than they look on a map. Five days is enough for the main highlights if you follow one clear route from east to west. Seven to ten days feels more relaxed.
Two main airports serve the island: Catania in the east and Palermo in the northwest. Flying into Catania works well if you start in Taormina, about an hour away. From mainland Italy, a short ferry crosses from Villa San Giovanni to Messina.
A rental car is the best way to get around, especially for small towns such as Ragusa and Modica. It also lets you stop at viewpoints and villages along the way. Buses and trains work in larger cities, but connections between towns can be slow.
The best months are late April to June and September to October, when the weather is mild and the sights are less crowded. July and August can be very hot and busy. Winter is quiet, but some small restaurants and shops have shorter hours.
Stay overnight along the route in Taormina, Syracuse, Agrigento, and Palermo instead of driving back to one base.
On day one, start in Taormina. Walk along Corso Umberto, visit the ancient Greek theater, Teatro Antico, and stop at Isola Bella for a swim. On the way to Etna, see the volcanic rock gorges of Gole Alcantara. In the afternoon, drive up Mount Etna, where a cable car from Rifugio Sapienza takes you higher. Return to Taormina for the night.
On day two, explore Catania, with its fish market and Via Etnea, then continue to Syracuse. Visit the Neapolis Archaeological Park and spend the evening in Ortigia, the old town, with its narrow streets and sea views.
On day three, drive through the baroque towns of southeastern Sicily: Noto for its cathedral square, Modica for its chocolate, and Ragusa for its old district, Ragusa Ibla. Then continue to Agrigento for the night.
On day four, visit the Valley of the Temples early, before it gets hot. The Temple of Concordia is one of the best-preserved Greek temples in the world. Then drive to Cefalù, a seaside town with a cathedral, and continue west to Palermo for the night.
Spend your last day in Palermo. See the Palazzo dei Normanni, the cathedral, and Quattro Canti, and try street food in the markets. One day covers the main sights, but two days is better if you can.